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Chemistry: Principles and Practice

Chemistry: Principles and Practice

3rd Edition

ISBN:9780534420123

Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer

Publisher:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer

Chapter9: Chemical Bonds

Section: Chapter Questions

Problem 9.68QE

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Consider the following structure:
i
Part 1 of 2
How many additional reasonable resonance structure(s) can be drawn for the given structure?
3
Part 2 of 2
Draw the structure(s) for all the additional reasonable resonance structure(s). Be sure to include lone pairs and

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Given the bonds C N, C H, C Br, and S O, (a) which atom in each is the more electronegative? (b) which of these bonds is the most polar?
Write all possible resonance structures for the following species. Assign a formal charge to each atom. In each case, which resonance structure is the most important? (a) NO2 (nitrogen is central) (b) ClCN
Three known isomers exist of N2CO, with the atoms in these sequences: NOCN; ONNC; and ONCN. Write resonance structures for each isomer and use formal charge to predict which isomer is the most stable.
Write all resonance structures of chlorobenzene, C6H5Cl, a molecule with the same cyclic structure as benzene. In all structures, keep the CCl bond as a single bond. Which resonance structures are the most important?
Draw all resonance structures for methylisocyanate, CH3NCO, a toxic gas used in the manufacturing of pesticides. Which resonance structures are the most important?
Consider the pyrosulfate ion, S2O72-. It has no sulfurâ€“sulfur nor oxygenâ€“oxygen bonds. (a) Write a Lewis structure for the pyrosulfate ion using only single bonds. (b) What is the formal charge on the sulfur atoms for the Lewis structure you drew in part (a)? (c) Write another Lewis structure using six bonds and two Oâ€”S bonds. (d) What is the formal charge on each atom for the structure you drew in part (c)?
Using the bond dissociation enthalpies in Table 8.8, estimate the enthalpy of combustion of gaseous methane, CH4, to give water vapor and carbon dioxide gas.
Three resonance forms can be drawn for the molecule N2O. Which resonance form is likely to more closely resemble the structure of this molecule? (a) (b) (c)
Based on the concept of formal charge, what is the central atom in (a) HCN (do not include H as a possibility)? b) NOCI (Cl is always a terminal atom)?
A common trait of simple organic compounds is to have Lewis structures where all atoms have a formal charge of zero. Consider the following incomplete Lewis structure for an organic compound called methyl cyanoacrylate, the main ingredient in Super Glue. Draw a complete Lewis structure for methyl cyanoacrylate in which all atoms have a formal charge of zero.
Formamide, HC(O)NH2, is prepared at high pressures from carbon monoxide and ammonia, and serves as an industrial solvent (the parentheses around the O indicate that it is bonded only to the carbon atom and that the carbon atom is also bonded to the H and the N atoms). Two resonance forms (one with formal charges) can be written for formamide. Write both resonance structures, and predict the bond angles about the carbon and nitrogen atoms for each resonance form. Are they the same? Describe how the experimental determination of the HNH bond angle could be used to indicate which resonance form is more important.
Consider the following compounds: CO2, SO2, KrF2, SO3, NF3, IF3, CF4, SF4, XeF4, PF5, TF5, and SCl6. These 12 compounds are all examples of different molecular structures. Draw the Lewis structures for each and predict the molecular structures. Predict the bond angles and the polarity of each. (A polar molecule has a net dipole moment, while a nonpolar molecule does not.) See Exercises 25 and 26 for the molecular structures based on the trigonal bipyramid and the octahedral geometries.

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